The present invention relates to an arthropod-controlling composition comprising a specific xcex1-pyrone compound as an active ingredient.
Many arthropod-controlling compositions are on the market at present. However, the objected harmful arthropods have many kinds and the situations for controlling them are in many ways. Therefore, the arthropod-controlling composition having practically high effectiveness and safety is desired.
Though pyrethroid pesticides having rapid knock-down efficacy are excellent agents for controlling harmful insects, progress of pyrethroid resistance to some insects has been reported in various places recently. Under these circumstances, non-pyrethroid compounds having excellent knock-down efficacy are earnestly desired.
On the other hand, it is known that some xcex1-pyrone compounds are effective for controlling harmful acarina and insects such as housefly in Japanese Unexamined Patent Publication No. sho-51-19126. However, the compounds described in the publication do not necessarily give a sufficient effect.
The present invention provides an arthropod-controlling composition comprising an xcex1-pyrone compound (hereinafter, referred to as the Pyrone Compound) shown by formula: 
as an active ingredient, and the composition has an extremely high knock-down activity against harmful arthropods.
Examples of the arthropods against which the arthropod-controlling composition of the present invention exhibits a controlling effect include the following harmful insects, acarina, Diplopoda, Chilopoda and Isopoda:
Hemiptera:
Delphacidae (planthoppers) such as Laodelphax striatellus (small brown planthopper), Nilaparvata lugens (brown planthopper) and Sogatella furcifera (white-backed rice planthopper); Deltocephalidae (leafhoppers) such as Nephotettix cincticeps (green rice leafhopper), Recilia dorsalis (zig-zag rice leaf hopper) and Nephotettix virescens (green rice leafhopper), Aphididae (aphids) such as cotton aphid (Aphis gossypii); stink bugs; Aleyrodidae (whiteflies) such as Bemisia argentifolii; scales; Tingidae (lace bugs); Psyllidae (suckers) and so on.
Lepidoptera:
Pyralidae such as Chilo suppressalis (rice stem borer), Cnaphalocrocis medinalis (rice leafroller) and Plodia interpunctella (Indian meal moth); Noctuidae such as Spodoptera litura (tobacco cutworm), Pseudaletia separata (rice armyworm), Mamestra brassicae (cabbage armyworm), Agrotis spp. (e.g. Agrotis segetum (turnip cutworm), Agrotis ipsilon (black cutworm)), Helicoverpa spp., Heliothis spp. and Plusiinae; Pieridae such as Pieris rapae crucivora (common cabbageworm); Tortricidae such as Adoxophyes spp. (e.g. Adoxophyes orana fasciata); Carposinidae such as Carposina niponensis (peach fruit moth); Lyonetiidae; Lymantriidae; Plutellidae such as Plutella xylostella (diamondback moth); Hesperiidae such as Parnara guttata (rice skipper); Tineidae such as Tinea pellionella (casemaking clothes moth) and Tineola bisselliella (webbing clothes moth) and so on.
Diptera:
Culicidae (mosquitoes) such as Culex spp. (e.g. Culex pipiens pallens (common mosquito), Culex tritaeniorhynchus), Aedes spp. (e.g. Aedes aegypti (yellow fever mosquito), Aedes alhopictus) and Anopheles spp. (e.g. Anopheles sinensis); Chironomidae (midges); Muscidae such as Musca domestica (housefly), Muscina stabulans (false stablefly) and Fannia canicularis (little housefly); Calliphoridae; Sarcophagidae; Anthomyiidae such as Delia platura (seedcorn maggot) and Delia antiqua (onion maggot); Tephritidae (fluit flies); Drosophilidae; Psychodidae (moth flies); Tabanidae; Simuhidae (black flies); Stomoxyidae; Phoridae; Ceratopogonidae (biting midges) and so on.
Coleoptera (Beetles):
Scarabaeidae (scarabs) such as Anomala cuprea (cupreous chafer) and Anomala rufocuprea (soybean beetle); Curculionidae (weevils) such as Sitophilus zeamais (maize weevil), Lissorhoptrus oryzophilus (ricewater weevil), ball weevil and Callosobruchus chinensis (adzuki bean weevil); Dermestidae such as Authrenus verbasci (varied carpet beetle) and Attagenus unicolor japonicus (black carpet beetle); Tenebrionidae (darkling beetles) such as Tenebrio molitor (yellow mealworm) and Triboium castaneum (red flour beetle); Chrysomelidae (leaf beetles) such as Oulema oryzae (rice leaf beetle), Phyllotreta striolata (striped flea beetle) and Aulacophora femoralis (cucurbit leaf beetle); Corn rootworms such as Diabrotica virgifera (western corn rootworm) and Diabrotica undecimpunctata howardi (southern corn rootworm); Anobiidae; Coccinellidae (ladybirds) such as Epilachna spp. (e.g. Epilachna vigintioctopunctata (twenty-eight-spotted ladybird)); Lyctidae (powderpost beetles); Bostrychidae (false powderpost beetles); Cerambycidae; Staphylinidae such as Paederus fuscipes (robe beetle) and so on.
Dictyoptera:
Blattella germanica (German cockroach); Periplaneta fuliginosa (smokybrown cockroach); Periplaneta americana (American cockroach); Periplaneta brunnea (brown cockroach); Blatta orientalis (oriental cockroach) and so on;
Thysanoptera (Thrips):
Thrips palmi, western flower thrips, Thrips hawaiiensis (flower thrips) and so on.
Hymenoptera:
Formicidae (ants) such as Formica japonica, field ant (Lasius fuliginosus), little red ant (Monomorium pharaonis), little ant (Monomorium nipponensis) and pavement ant (Teramorium caespitum); Vespidae (hornets); Polistes spp. (long-legged wasps); Bethylidae; Tenthredinidae (sawflies) such as Athalis rosae ruficornis (cabbage sawfly) and so on.
Orthoptera:
Gryllotalpidae (mole crickets); Acrididae (grasshoppers) and so on.
Siphonaptera Pests (Fleas):
Ctenocephalides canis (dog flea); Ctenocephalides felis (cat flea); Pulex irritans and so on.
Anoplura (Lice):
Pediculus corporis; Pediculus humanus (body louse); Pthirus pubis (crab louse) and so on.
Isoptera:
Reticulitermes speratus; Coptotermes formosanus and so on.
Tetranychidae (Spider Mites):
Tetranychus cinnabarinus (carmine spider mite); Tetranychus urticae (two-spotted spider mite); Tetranychus kanzawai (Kanzawa spider mite); Panonychus citri (citrus red mite); Panonychus ulmi (European red mite) and so on.
Ixodidae:
Boophilus microplus; Haemaphysalis longiconis and so on
House-Dust Mites:
Acaridae such as Tyrophagus putrescentiae (copra mite) and Aleuroglyphus ovatus (brown legged grain mite); Dermanyssidae such as Dermatophagoides farinae (American house dust mite) and Dermatophagoides pteronyssinus; Glycyphagidae such as Glycyphagus privatus, Glycyphagus domesticus and Glycyphagus destructor; Cheyletidae such as Chelacaropsis malaccensis and Cheyletus fortis; Tarsonemidae; Chortoglyphus spp.; Haplochthonius spp. and so on.
Diplopoda (Milpedes):
Chilognatha such as Oxydus spp. and so on.
Chilopoda (Centipedes):
Scolopendra suhspinipes mutilans, red centipede and so on.
Isopoda:
Oniscoidea (pill bugs) such as Porcellio spp. (e.g. Porcellio scaber), Porcellionides spp. and Armadillidium spp. (e.g. Armadillium vulgare) and so on.
The Pyrone Compound can be prepared according to the procedure below:
Preparation of the Pyrone Compound
Ten grams (10.0 g, 79.3 mmol) of 4-hydroxy-6-methyl-2-pyrone were suspended in 100 ml of toluene at room temperature. To the suspension, 1.22 g (10.0 mmol) of N,N-dimethylaminopyridine, 10.0 g (86.1 mmol) of isocaproic acid and 18.5 g (89.7 mmol) of dicyclohexylcarbodiimide were added subsequently. The mixed solution was stirred for one hour at room temperature, and then heated to 70xc2x0 C. and stirred for 20 hours under heating. After the mixed solution was allowed to stand at room temperature, the precipitated insoluble dicyclohexylurea was filtered off, and washed with 1N hydrochloric acid once and 10% (by weight) brine twice. The organic layer collected from the filtrate was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give a crude oily product.
The oily product was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=6/1) to give 7.11 g of the Pyrone Compound (yield 40%).
1H-NMR (CDCl3/TMS): 0.94 (6H, d), 1.54 (2H, q), 1.63 (1H, m), 2.27 (3H, s), 3.08 (2H, t), 5.93 (1H, s), 17.88 (1H, s)
The Pyrone Compound utilized in the present invention is a compound of formula: 
wherein R represents a group of xe2x80x94CH2CH2CH(CH3)2, having an NMR spectrum described above and melting point of 42xc2x0 C.
The arthropod-controlling composition of the present invention comprises the Pyrone Compound as an active ingredient and an inert carrier. The content of the Pyrone Compound in the arthropod-controlling composition is an effective amount, usually 0.001 to 95% by weight. The arthropod-controlling composition is usually to be formulated as described below for use.
The Pyrone Compound can be formulated to the present composition such as oil solution, emulsifiable concentrate, wettable powder, flowable (aqueous suspension or aqueous emulsion), granule, dust and so on, by mixing with solid carrier, liquid carrier or gaseous carrier and optionally surfactant, the other formulation additive.
Examples of the solid carrier used in the formulation described above include inorganic carriers such as clays (e.g. kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, Fubasami clay, acid clay), talc, ceramics, sericite, quartz and calcium carbonate. Examples of the liquid carrier include water, alcohols (e.g. methanol, ethanol, higher alcohols), ketones (e.g. acetone, methyl ethyl ketone), aromatic hydrocarbons (e.g. benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (e.g. hexane, cyclohexane, kerosine, gas oil), esters (ethyl acetate, butyl acetate), nitrites (e.g. acetonitrile, isobutyronitrile), ethers (e.g. diisopropyl ether, dioxane), acid amides (e.g. N,N-dimethylformamide, N,N-dimethylacetamide), halogenated hydrocarbons (e.g. dichloromethane, trichloroethane, carbon tetrachloride), dimethyl sulfoxide and vegetable oils (e.g. soybean oil, cottonseed oil). Examples of the liquefied gaseous carrier include fluorocarbon, fluorohydrocarbon, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.
Examples of the surfactant optionally used in the formulation include alkyl sulfate salts, alkylsulfonate salts, alkylarylsulfonate salts, alkyl aryl ethers, polyoxyethylenealkyl aryl ethers, polyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives.
The other formulation auxiliaries are exemplified by sticking agent, dispersant and stabilizer. Examples of sticking agent and dispersant include casein, gelatin, polysaccharides (e.g. starch powder, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, sugars and synthetic water-soluble polymers (e.g. polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids). Examples of stabilizer include phenol type antioxidants such as BHT (2,6-di-tert-butyl-4-methyphenol) and BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), amine type antioxidants such as diphenylamine, organic sulfur type antioxidants such as 2-mercaptobenzimidazole, PAP (acid isopropyl phosphate), vegetable oils, mineral oils, surfactants, fatty acids and esters of fatty acid.
The flowable formulations (aqueous suspension or aqueous emulsion) usually comprise the Pyrone Compound, dispersant, suspension assistant (for example, protective colloid or a compound giving thixotropy), suitable auxiliaries (for example, antifoamer, rust preventive agent, stabilizer, developing agent, penetrating assistant, antifreezing agent, bactericide, fungicide, etc.) and water. Examples of the protective colloid include gelatin, casein, gums, cellulose ethers and polyvinyl alcohol, and examples of the compound giving thixotropy include bentonite, aluminum magnesium silicate, xanthan gum and polyacrylic acids. Use of the oil which can rarely dissolve the Pyrone Compound in place of water can give suspension-in-oil formulation.
The formulations of emulsifiable concentrate, wettable powder, flowable and so on obtained above are usually diluted with water and so on, and applied at 0.1 to 10000 ppm of the concentration of the Pyrone Compound. The formulations of oil solution, granule, dust and so on are usually applied as they are.
Further, the Pyrone Compound or its formulation can be used after making the forms below.
A mixture of the Pyrone Compound or its liquid formulation and a propellant can be charged into a pressure container with a spray nozzle to afford an aerosol of the present controlling agent. Further, the Pyrone Compound or its liquid formulation can be impregnated into a base material of mosquito-coil, mosquito-mat, ceramic board and so on to afford a heating volatile formulation such as mosquito-coil and mosquito-mat for electric heater; a heating fumigant formulation such as self-combustible fumigant, chemical reaction type fumigant and porous ceramic board fumigant; a non-heating volatile formulation such as resin volatile formulation and paper volatile formulation; a smoking formulation such as fogging; and an ULV formulation of the present controlling agent. Furthermore, a liquid formulation of the Pyrone Compound can be charged into a container with an absorptive wick in the upper part to afford a bottle containing insecticidal liquid for volitilization by heating the absorptive wick.
Examples of the propellant for aerosols include propane, butane, isobutane, dimethyl ether, methyl ethyl ether and methylal.
An example of the base material of the mosquito-coil is a mixture of raw plant powder such as wood powder and Pyrethrum marc and a binding agent like Tabu powder (powder of Machilus thunbergii), starch or gluten.
Examples of the base material of the mosquito-mat for electric heating fumigation include a plate of compacted fibrils of cotton linters and a mixture of pulp and cotton linters.
The base material of the self-combustible fumigant includes, for example, an exothermic agent (e.g. nitrate, nitrite, guanidine salt, potassium chlorate, nitrocellulose, ethylcellulose, wood powder), a pyrolytic stimulating agent (e.g. alkali metal salt, alkaline earth metal salt, dichromate, chromate), an oxygen source (e.g. potassium nitrate), a combustion assistant (e.g. melanin, wheat starch), a bulk filler (e.g. diatomaceous earth) and a binding agent (e.g. synthetic glue).
The base material of the chemical reaction type fumigant includes, for example, an exothermic agent (e.g. alkali metal sulfide, polysulfide, hydrogensufide and hydrated salt, calcium oxide), a catalytic agent (e.g. carbonaneous substance, iron carbide, activated clay), an organic foaming agent (e.g. azodicarbonamide, benzenesulfonylhydrazide, dinitrosopentamethylenetetramine, polystyrene, polyurethane, etc.) and a filler (e.g. natural or synthetic fibers).
An example of the base material of the resin volatile formulation is thermoplastic resin, and examples of the base material of the paper volatile formulation include filter paper and Japanese paper.
The present arthropod-controlling composition can be used simultaneously with the other insecticide, the other acaricide, repellent or synergist under non-mixed conditions or pre-mixed conditions.
Examples of the insecticides and acaricides include organophosphorus compounds such as fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate], fenthion [O,O-dimethyl O-(3-methyl-4-(methythio)phenyl) phosphorothioate], diazinon [O,O-diethyl O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate], chlorpyrifos [O,O-diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate], DDVP [2,2-dichlorovinyl dimethyl phosphate], cyanophos [O-4-cyanophenyl O,O-dimethyl phosphorothioate], dimethoate [O,O-dimethyl S-(N-methylcarbamoylmethyl) dithiophosphate], phenthoate [ethyl 2-dimethoxyphosphinothioylthio(phenyl)acetate], malathion [diethyl (dimethoxyphosphinothioylthio)succinate], and azinphos-methyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O,O-dimethyl phosphorodithioate]; carbamate compounds such as BPMC (2-sec-butylphenyl methylcarbamate), benfracarb [ethyl N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl (methyl)aminothio]-N-isopropyl-xcex2-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate] and carbaryl [1-naphthyl-N-methylcarbamate], methomyl [S-methyl-N-[(methylcarbamoyl)oxy]thioacetimidate]; pyrethroid compounds such as etofenprox [2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate], esfenvalerate [(S)-xcex1-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate], fenpropathrin [(RS)-xcex1-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], cypermethrin [(RS)-xcex1-cyano-3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], cyhalothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S)-xcex1-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate], cycloprothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], fluvalinate [xcex1-cyano-3-phenoxybenzyl N-(2-chloro-xcex1,xcex1,xcex1-trifluoro-p-tolyl)-D-valinate], bifenthrin [2-methylbiphenyl-3-ylmethyl (Z)-(1RS)-cis-3-(2-chloro-3,3, 3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], 2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl 3-phenoxybenzyl ether, tralomethrin [(S)-xcex1-cyano-3-phenoxybenzyl (1R-cis)-3-{(1RS)(1,2,2,2-tetrabromoethyl)}-2,2-dimethylcyclopropanecarboxylate], silafluofen [(4-ethoxyphenyl){3-(4-fluoro-3-phenoxyphenyl)propyl}dimethylsilane], d-phenothrin [3-phenoxybenzyl (1R-cis,trans)-chrysanthemate], cyphenothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (1R-cis,trans)-chrysanthemate], d-resmethrin [5-benzyl-3-furylmethyl (1R-cis,trans)-chrysanthemate], acrinathrin [(S)-xcex1-cyano-3-phenoxybenzyl (1R,cis(Z))-2,2-dimethyl-3-{3-oxo-3-(1,1,1,3,3,3-hexafluoropropyloxy)propenyl}cyclopropanecarboxylate], cyfluthrin [(RS)-xcex1-cyano-4-fluoro-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], tefluthrin [2,3,5,6-tetrafluoro-4-methylbenzyl (1RS-cis(Z))-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], transfluthrin [2,3,5,6-tetrafluorobenzyl (1R-trans)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], tetramethrin [3,4,5,6-tetrahydrophthalimidomethyl (1RS)-cis,trans-chrysanthemate], allethrin [(RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS)-cis,trans-chrysanthemate], prallethrin [(S)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1R)-cis,trans-chrysanthemate], empenthrin [(RS)-1-ethynyl-2-methyl-2-pentenyl (1R)-cis, trans-chrysanthemate], imiprothrin [2,5-dioxo-3-(prop-2-ynyl)imidazolidin-1-ylmethyl (1R)-cis,trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate], d-furamethrin [5-(2-propynyl)furfuryl (1R)-cis,trans-chrysanthemate] and 5-(2-propynyl)furfuryl 2,2,3,3-tetramethylcyclopropanecarboxylate; nitroimidazoliiine derivatives such as imidacioprid (1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine); N-cyanoamidine derivatives such as N-cyano-Nxe2x80x2-methyl-Nxe2x80x2-(6-chloro-3-pyridylmethyl)acetamidine; nitenpyram [N-(6-chloro-3-pyridylmethyl)-N-ethyl-N-methyl-2-nitrovynylidenediamine]; thiacloprid [1-(2-chloro-5-pyridylmethyl)-2-cyanoiminothiazoline]; thiamethoxam [3-((2-chloro-5-thiazolyl) methyl)-5-methyl-4-nitroiminotetrahydro-1,3,5-oxadiazine]; 1-methyl-2-nitro-3-((3-tetrahydrofuryl)methyl)guanidine; 1-(2-chloro-5-thiazolyl)methyl-3-methyl-2-nitroguanidine; nitroiminohexahydro-1,3,5-triazine derivatives; chlorinated hydrocarbons such as endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine oxide], xcex3-BHC [1,2,3,4,5,6-hexachlorocyclohexane] and 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol; benzoylphenylurea compounds such as chlorfluazuron [1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridyn-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl)urea], teflubenzuron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea] and flufenoxuron [1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)urea]; juvenile hormone like compounds such as pyriproxyfen [4-phenoxyphenyl 2-(2-pyridyloxy)propyl ether], methoprene [isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate] and hydroprene [ethyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate]; thiourea derivatives such as diafenthiuron [N-(2,6-diisopropyl-4-phenoxyphenyl)-Nxe2x80x2-tert-butylcarbodiimide]; phenylpyrazole compounds; 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrol-3-carbonitrile [chlorfenapil]; metoxadiazone [5-methoxy-3-(2-methoxyphenyl)-1,3,4-oxadiazol-2(3H)-one], bromopropylate [isopropyl 4,4-dibromobenzilate], tetradifon [4-chlorophenyl 2,4,5-trichlorophenyl sulfone], chinomethionat [S,S-6-methylquinoxaline-2,3-diyldithiocarbonate], pyridaben [2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one], fenpyroximate [tert-butyl (E)-4-[(1, 3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl]benzoate], tebufenpyrad [N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide], polynactins complex [tetranactin, dinactin and trinactin], pyrimidifen [5-chloro-N-[2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxy}ethyl]-6-ethylpyrimidin-4-amine], milbemectin, abamectin, ivermectin and azadirachtin [AZAD]. Examples of the repellants include 3,4-carane-diol, N,N-diethyl-m-toluamide, 1-methylpropyl 2-(2-hydroxyetnyl)-1-piperidinecarboxylate, p-menthane-3,8-diol and plant essential oil such as hyssop oil, and examples of the synergists include bis-(2,3,3,3-tetrachloropropyl) ether (S-421), N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide (MGK-264) and xcex1-[2-(2-butoxyethoxy)ethoxy]-4,5-methylenedioxy-2-propyltoluene (piperonyl butoxide).
The application amount and concentration of the present controlling agent can be suitably designed according to the type of the formulations, time, place, and method of application, kind of harmful arthropods and damage.
The present compound can exhibit its more excellent pesticidal effect under heating or non-heating volatilation. Therefore, it is especially useful as an active ingredient of household pesticide.